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Wind Surf
Windstar Cruises
Jan 23, 2027 - Jan 30, 2027 (7 Nights)
Philipsburg, St. Maarten • Charlestown, Nevis • Roseau, Dominica • Mayreau Island, Saint Vincent and the Grenadines • Les Saintes, F.W.I. • Basseterre, St. Kitts and Nevis • Gustavia, St. Barts • Philipsburg, St. Maarten
Average Starting Price
$3,272pp
Jim's Onboard Credit
Seabourn Ovation
Seabourn
Feb 3, 2029 - Feb 24, 2029 (21 Nights)
Bridgetown, Barbados • Rodney Bay, Saint Lucia • Willemstad, Curacao • Oranjestad, Aruba • Kralendijk, Bonaire • Bridgetown, Barbados • Bequia Island, Saint Vincent • Trois Ilets, Martinique • St John's, Antigua • St. Kitts • Great Harbor Jost Van Dyke, British Virgin Islands • Philipsburg, St. Maarten • St. Kitts • Saint Barthelemy, Gustavia • Castries, St. Lucia • Terre de Haut, Guadeloupe • Grenada • Bridgetown, Barbados
Average Starting Price
$14,378pp
Jim's Onboard Credit
49% OFF
MSC Opera
MSC Cruises
Dec 27, 2027 - Jan 10, 2028 (14 Nights)
La Romana, Dominican Republic • Catalina Island, Dominican Republic • Virgin Gorda, British Virgin Islands • Philipsburg, St. Maarten • St. Kitts • St John's, Antigua • La Romana, Dominican Republic • Catalina Island, Dominican Republic • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Grenada • La Romana, Dominican Republic
Average Starting Price
$2,482pp
Jim's Onboard Credit

Phyllis' Holiday Pick
Best time of the year to cruise! I love spending the holidays cruising with my family! The ships are beautifully decorated, and ringing in New Year’s Eve at sea is an experience I’ll never forget!

Wind Surf
Windstar Cruises
Mar 19, 2028 - Apr 11, 2028 (23 Nights)
Philipsburg, St. Maarten • Porto Santo (Madeira), Portugal • Funchal, Portugal • Lisbon, Portugal • Cadiz, Spain • Gibraltar • Malaga, Spain • Almeria, Spain • Cartagena, Spain • Palma de Mallorca, Spain • Barcelona, Spain
Average Starting Price
$5,689pp
Jim's Onboard Credit
Seabourn Ovation
Seabourn
Dec 19, 2026 - Dec 26, 2026 (7 Nights)
Bridgetown, Barbados • Castries, St. Lucia • Little Bay, Montserrat • St John's, Antigua • St. Kitts • Great Harbor Jost Van Dyke, British Virgin Islands • Philipsburg, St. Maarten
Average Starting Price
$3,773pp
Jim's Onboard Credit

Phyllis' Holiday Pick
Best time of the year to cruise! I love spending the holidays cruising with my family! The ships are beautifully decorated, and ringing in New Year’s Eve at sea is an experience I’ll never forget!

54% OFF
MSC Opera
MSC Cruises
Mar 29, 2027 - Apr 5, 2027 (7 Nights)
La Romana, Dominican Republic • Catalina Island, Dominican Republic • Virgin Gorda, British Virgin Islands • Philipsburg, St. Maarten • St. Kitts • St John's, Antigua • La Romana, Dominican Republic
Average Starting Price
$679pp
Jim's Onboard Credit
Wind Surf
Windstar Cruises
Mar 19, 2028 - Apr 3, 2028 (15 Nights)
Philipsburg, St. Maarten • Horta (Azores), Portugal • Ponta Delgada (Azores), Portugal • Lisbon, Portugal
Average Starting Price
$2,580pp
Jim's Onboard Credit
Seabourn Ovation
Seabourn
Mar 17, 2029 - Mar 24, 2029 (7 Nights)
Philipsburg, St. Maarten • St. Kitts • Saint Barthelemy, Gustavia • Castries, St. Lucia • Terre de Haut, Guadeloupe • Grenada • Bridgetown, Barbados
Average Starting Price
$5,343pp
Jim's Onboard Credit
50% OFF
MSC Opera
MSC Cruises
Dec 20, 2027 - Jan 3, 2028 (14 Nights)
La Romana, Dominican Republic • Catalina Island, Dominican Republic • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Grenada • La Romana, Dominican Republic • Catalina Island, Dominican Republic • Virgin Gorda, British Virgin Islands • Philipsburg, St. Maarten • St. Kitts • St John's, Antigua • La Romana, Dominican Republic
Average Starting Price
$2,692pp
Jim's Onboard Credit

Phyllis' Holiday Pick
Best time of the year to cruise! I love spending the holidays cruising with my family! The ships are beautifully decorated, and ringing in New Year’s Eve at sea is an experience I’ll never forget!

Wind Surf
Windstar Cruises
Jan 16, 2027 - Jan 23, 2027 (7 Nights)
Philipsburg, St. Maarten • Road Bay, Anguilla • Soper's Hole, Tortola • Great Harbor Jost Van Dyke, British Virgin Islands • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • Gustavia, St. Barts • Falmouth (English Harbour), Antigua & Barbuda • Philipsburg, St. Maarten
Average Starting Price
$3,288pp
Jim's Onboard Credit
Seabourn Ovation
Seabourn
Dec 9, 2028 - Dec 23, 2028 (14 Nights)
Bridgetown, Barbados • Bequia Island, Saint Vincent • Trois Ilets, Martinique • St John's, Antigua • St. Kitts • Great Harbor Jost Van Dyke, British Virgin Islands • Philipsburg, St. Maarten • St. Kitts • Saint Barthelemy, Gustavia • Castries, St. Lucia • Terre de Haut, Guadeloupe • Grenada • Bridgetown, Barbados
Average Starting Price
$8,608pp
Jim's Onboard Credit
55% OFF
MSC Opera
MSC Cruises
Mar 15, 2027 - Mar 22, 2027 (7 Nights)
La Romana, Dominican Republic • Virgin Gorda, British Virgin Islands • Philipsburg, St. Maarten • St. Kitts • Tortola • Catalina Island, Dominican Republic • La Romana, Dominican Republic
Average Starting Price
$569pp
Jim's Onboard Credit
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